JPH0624967A - Substance having mutagen-suppressing action - Google Patents

Substance having mutagen-suppressing action

Info

Publication number
JPH0624967A
JPH0624967A JP4083370A JP8337092A JPH0624967A JP H0624967 A JPH0624967 A JP H0624967A JP 4083370 A JP4083370 A JP 4083370A JP 8337092 A JP8337092 A JP 8337092A JP H0624967 A JPH0624967 A JP H0624967A
Authority
JP
Japan
Prior art keywords
substance
mutagen
trihydroxystilbene
concentration
suppressing action
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
JP4083370A
Other languages
Japanese (ja)
Other versions
JP2562092B2 (en
Inventor
Fukuji Kaminobu
富久治 上延
Seiichi Nakamura
清一 中村
Shinichi Nagai
岑一 永井
Masakazu Shioyama
正和 塩山
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Yushiro Chemical Industry Co Ltd
Original Assignee
Yushiro Chemical Industry Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Yushiro Chemical Industry Co Ltd filed Critical Yushiro Chemical Industry Co Ltd
Priority to JP4083370A priority Critical patent/JP2562092B2/en
Publication of JPH0624967A publication Critical patent/JPH0624967A/en
Application granted granted Critical
Publication of JP2562092B2 publication Critical patent/JP2562092B2/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02ATECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

PURPOSE:To obtain a substance containing 3,4',5-trihydroxystilbene, having a simple structure and excellent mutagen-suppressing action. CONSTITUTION:An agent contains 0.2-0.4mg/ml 3,4',5-trihydroxystilbene. This substance exhibits strong suppressing action on induction of SOS reaction due to activated Trp-p-1. The concentration of the substance exhibits a positively proportional relationship to SOS reaction suppressive ratio and exhibits 72% SOS reaction suppressive ratio at 0.3mg/ml content and 98% SOS reaction suppressive ratio at 0.4mg/ml content. This substance can be expected as a carcinostatic substance.

Description

【発明の詳細な説明】Detailed Description of the Invention

【0001】[0001]

【産業上の利用分野】本発明は、3,4′,5−トリヒ
ドロキシスチルベンからなる変異原抑制作用を有する物
質に関する。
BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a substance consisting of 3,4 ', 5-trihydroxystilbene which has a mutagen inhibiting effect.

【0002】[0002]

【従来の技術】従来、植物より抽出した抽出物からなる
発癌抑制物質に関しては、多くの研究が行われており、
単子葉植物からの抽出物として、イネ科植物、ユリ科植
物、或いはあやめ科植物起源のものが知られている。例
えば、ユリ科植物起源に於いては、南アフリカ産ケープ
アロエ葉(特公昭46−28092号)、にんにく或い
はたまねぎ等(特開昭48−98010号、特開昭48
−98011号)が、あやめ科植物起源のものに於いて
は、トリトーニア属植物を原料とするもの(特公昭54
−28806号)が知られている。更に、この他にも、
薬用ニンジンから抽出される成分(特開昭55−334
56号)、キク科植物に属するひよどりばなの抽出物
(特開昭55−45652号)、アマチャヅルから抽出
される成分(特開昭58−59921号)、サイコ中に
含まれる成分(特開昭62−187408号)等のサポ
ニンを含む抽出物が制癌効果を有している物質として知
られている。
2. Description of the Related Art Conventionally, many studies have been carried out on a carcinogenic inhibitory substance consisting of an extract extracted from a plant,
As an extract from a monocotyledonous plant, a plant of Gramineae plant, Liliaceae plant, or Iridaceae plant origin is known. For example, in the origin of the Liliaceae plant, Cape Aloe leaves from South Africa (Japanese Patent Publication No. 46-28092), garlic or onions (Japanese Patent Laid-Open Nos. 48-98010 and 48).
-98011), which originates from the plant of the genus Tritonia, in the case of the origin of the iris family (JP-B-54
No. 28806) is known. In addition to this,
Ingredients extracted from medicinal carrot (JP-A-55-334)
56), an extract of Hiyodoribana belonging to the Asteraceae plant (Japanese Patent Laid-Open No. 55-45652), a component extracted from Achachatsuru (Japanese Patent Laid-Open No. 58-59921), and a component contained in Psycho (Japanese Laid-Open Patent Publication No. 62-187408) and other extracts containing saponins are known as substances having an anti-cancer effect.

【0003】また、制癌作用をもつスチルベン誘導体と
しては、4,4’−ビス(1・3・5−トリアジル−6
−アミノ)スチルベン−2・2’−ジスルホン酸誘導体
が知られている(特公昭46−15503号公報)。
As a stilbene derivative having an antitumor effect, 4,4'-bis (13.5-triazyl-6) is used.
-Amino) stilbene-2,2'-disulfonic acid derivative is known (Japanese Patent Publication No. 46-15503).

【0004】[0004]

【発明が解決しようとする問題点】しかし、上記スチル
ベン誘導体は、大変複雑な構造を有し、その製造も大変
であり、もっと容易に製造若しくは抽出できる変異原抑
制作用を有する物質の現出が好ましい。本発明は、上記
観点に鑑みてなされたものであり、構造が簡単で且つ優
れた変異原抑制作用を有する物質を提供することを目的
とする。
However, the above-mentioned stilbene derivative has a very complicated structure, and its production is also difficult, and the appearance of a substance having a mutagen inhibitory effect that can be produced or extracted more easily has not been revealed. preferable. The present invention has been made in view of the above viewpoints, and an object thereof is to provide a substance having a simple structure and an excellent mutagen suppressing activity.

【0005】[0005]

【課題を解決するための手段】本発明者らは、変異原抑
制作用を有する物質について種々検討した結果、本発明
を完成するに至ったのである。即ち、本発明の変異原抑
制物質は、化1に示す3−4′−5−トリヒドロキシス
チルベン(以下、単に、トリヒドロキシスチルベンとも
いう。)からなることを特徴とする。ここで、「トリヒ
ドロキシスチルベンからなる」とは、トリヒドロキシス
チルベン単体のみならず、トリヒドロキシスチルベンを
含有する場合(例えば溶液、更に他の粉末を含む混合粉
末物等)をも含む意味に使用される。通常は、そのまま
の溶液を使用したり、使用直前に粉末等を所定溶媒に溶
解させて調製した溶液を使用する。
The present inventors have completed the present invention as a result of various studies on substances having a mutagen suppressing action. That is, the mutagen inhibitor of the present invention is characterized by being composed of 3-4'-5-trihydroxystilbene (hereinafter, also simply referred to as trihydroxystilbene) shown in Chemical formula 1. Here, the term “consisting of trihydroxystilbene” is used to mean not only trihydroxystilbene itself but also the case of containing trihydroxystilbene (eg, solution, mixed powder containing other powders, etc.). It Usually, a solution as it is is used, or a solution prepared by dissolving powder or the like in a predetermined solvent immediately before use is used.

【0006】[0006]

【化1】 [Chemical 1]

【0007】[0007]

【実施例】以下、実施例により本発明を具体的に説明す
る。本実施例は、表1及び下記に示す試料濃度の各試料
(S)を調製し、この試料の添加により、一定量の変異
原(活性化Trp−P−1)によるSOS反応の誘導がど
れくらい抑制されるかを、調べたものである。この抑制
効果は、SOS反応の誘導を指標とした変異原物質検出
法(umu試験)により調べた。ここで、「umu試
験」とは、大腸菌のDNA損傷時にみられるSOS反応
を利用した新しい型の変異原検出試験である。この試験
方法は、以下に述べるものであり、短時間で結果が出る
など多くの利点を備えている。即ち、LB培地(トリプ
トン1%、酵母エキス0.5%、食塩0.5%)にて3
7℃で一夜培養した試験菌液(試験菌 Salmonella ty
phimurium TA1535/pSK1002)をTGA培地(トリプトン
1%、食塩0.5%、グルコース0.2%にアンピシリ
ンを50μg/mlの割で加えたもの)に1/50量植
菌し、37℃で振とう培養した。
EXAMPLES The present invention will be specifically described below with reference to examples. In this example, each sample (S) having the sample concentrations shown in Table 1 and the following was prepared, and addition of this sample caused induction of the SOS reaction by a certain amount of mutagen (activated T rp -P-1). I investigated how much it was suppressed. This inhibitory effect was examined by a mutagen detection method (umu test) using the induction of SOS reaction as an index. Here, the "umu test" is a new type of mutagen detection test that utilizes the SOS reaction that is observed during DNA damage in Escherichia coli. This test method is described below, and has many advantages such as results in a short time. That is, 3 in LB medium (tryptone 1%, yeast extract 0.5%, salt 0.5%)
Test bacterial solution (test bacteria Salmonella ty
phimurium TA1535 / pSK1002) was inoculated into TGA medium (1% tryptone, 0.5% salt, 0.2% glucose with ampicillin added at a rate of 50 μg / ml) and shaken at 37 ° C. Cultured.

【0008】そして、菌濃度が対数増殖期(A600
0.25〜0.30)に達したとき、菌液を2.0ml
ずつ試験管にとり、これに変異原物質(下記に示すよう
にして作成された活性化Trp−P−1)0.1ml、各
試料0.1ml、0.1Mリン酸緩衝液(pH7.0)
0.3mlを加えて、37℃で2時間培養した。培養後
に菌液を遠沈し集菌した後、菌を生理的食塩水に再懸濁
し、この菌液の一部で菌量を測定し、他の一部でβ−ガ
ラクトシダーゼ活性を測定した。尚、ここで、対数増殖
期とは、細菌や細胞の数が対数的に増加していく時期
で、指数増殖期ともいわれるものである。
When the bacterial concentration reaches the logarithmic growth phase (A 600 is 0.25 to 0.30), 2.0 ml of the bacterial solution is added.
Each of them was placed in a test tube, and 0.1 ml of a mutagen (activated T rp -P-1 prepared as shown below), 0.1 ml of each sample, and 0.1 M phosphate buffer (pH 7.0) were added. )
0.3 ml was added and the mixture was cultured at 37 ° C. for 2 hours. After culturing, the bacterial solution was spun down to collect the cells, and then the cells were resuspended in physiological saline, the bacterial amount was measured in a part of this bacterial solution, and the β-galactosidase activity was measured in another part. Here, the logarithmic growth phase is the time when the number of bacteria and cells increases logarithmically, and is also called the exponential growth phase.

【0009】β−ガラクトシダーゼ活性の測定は、Mill
erの方法(Miller, J. H:Experiments in molecular ge
netics, Coldspring Harbor Laboratory, NewYork,
P352-355 (1972))に準じて行った。即ち、Z緩衝液2.
25mlに上記試験菌液0.25mlを加えた後、0.
1%のsodium dodecyl sulfate水溶液50μl及びクロ
ロホルム10μlを加え強く攪拌した。その液に基質
(o-nitro-phenyl- β-D-galactopyranoside 4 mg/
ml) 0.25mlを加え、28℃で反応させた。そし
て、15分後1M Na2 CO3 を1.25ml加えて
反応を止め、分光光度計でA420 、A550 及びA
600 (吸光度)を測定した。
The β-galactosidase activity is measured by Mill
er's method (Miller, J. H: Experiments in molecular ge
netics, Coldspring Harbor Laboratory, New York,
P352-355 (1972)). That is, Z buffer 2.
After adding 0.25 ml of the above test bacterial solution to 25 ml,
50 μl of 1% aqueous solution of sodium dodecyl sulfate and 10 μl of chloroform were added and stirred vigorously. Substrate (o-nitro-phenyl-β-D-galactopyranoside 4 mg /
ml) 0.25 ml was added, and the mixture was reacted at 28 ° C. Then, after 15 minutes, 1.25 ml of 1 M Na 2 CO 3 was added to stop the reaction, and A 420 , A 550 and A were measured with a spectrophotometer.
600 (absorbance) was measured.

【0010】ここで、β−ガラクトシダーゼ活性値は、
次式により算出した。 β−ガラクトシダーゼ活性値(unit) =1000(A420
1.75×A550)/1.5×A600 また、SOS反応抑制率は、次式により算出した。 SOS反応抑制率(%)=〔1−(A−C)/(B−
C)〕×100(%) 但し、上式中Aは変異原物質に試料(S)を加えた場合
のβ−ガラクトシダーゼ活性値を、Bは変異原物質のみ
により誘導されたβ−ガラクトシダーゼ活性値を、Cは
コントロールのβ−ガラクトシダーゼ活性値をそれぞれ
示す。
Here, the β-galactosidase activity value is
It was calculated by the following formula. β-galactosidase activity value (unit) = 1000 (A 420
1.75 × A 550 ) /1.5×A 600 The SOS reaction inhibition rate was calculated by the following formula. SOS reaction suppression rate (%) = [1- (AC) / (B-
C)] × 100 (%) where A is the β-galactosidase activity value when the sample (S) is added to the mutagen, and B is the β-galactosidase activity value induced only by the mutagen. , C shows the control β-galactosidase activity value, respectively.

【0011】試料濃度は、上記試料(S)を10mg/
mlの濃度になるように純水に溶解したものを原液と
し、1mg(トリヒドロキシスチルベン)/2.5m
l、0.75mg/2.5ml、0.5mg/2.5m
lの3濃度(即ち、各々、0.4mg/ml、0.3m
g/ml、0.2mg/ml)になるように調製し、こ
の3濃度のサンプルについて調べた。コントロールには
同量の純水を使用した。各試験は試行を1組として行
い、その平均をとった。活性化Trp−P−1の作成は、
rp−P−1 5mgを20mlの純水に溶解し、これ
にS9mix 20mlを加えて37℃で培養した。20分
後に40mlのアセトンを加え反応を停止させ、遠心分
離により変性蛋白を除いた。この遠心上澄液を、氷冷下
でロータリーエバポレーターにより減圧・濃縮(アセト
ンを除いた)し、この濃縮液を活性化Trp−P−1とし
た。そして、表中の活性化Trp−P−1液はTrp−P−
1濃度を0.4mg/mlとしたものである。そして、
活性化Trp−P−1/トリヒドロキシスチルベン混合液
は、表中に示すトリヒドロキシスチルベン濃度及び0.
4mg/mlのTrp−P−1濃度を示す。以上の試験の
結果を表1に示す。
The sample concentration is 10 mg / sample of the above sample (S).
Dissolved in pure water to a concentration of ml to make a stock solution, 1 mg (trihydroxystilbene) /2.5 m
1, 0.75mg / 2.5ml, 0.5mg / 2.5m
3 concentrations of 1 (ie 0.4 mg / ml, 0.3 m, respectively)
g / ml, 0.2 mg / ml), and samples of these 3 concentrations were investigated. The same amount of pure water was used as a control. Each test was conducted as one set of trials, and the average thereof was taken. Creation of activated T rp -P-1
The T rp -P-1 5mg dissolved in pure water 20 ml, and cultured at 37 ° C. by adding S9mix 20 ml thereto. After 20 minutes, 40 ml of acetone was added to stop the reaction, and the denatured protein was removed by centrifugation. This centrifugal supernatant was decompressed and concentrated (without acetone) by a rotary evaporator under ice cooling, and this concentrated liquid was designated as activated T rp -P-1. The activated T rp -P-1 solution in the table is T rp -P-
One concentration was 0.4 mg / ml. And
The activated T rp -P-1 / trihydroxystilbene mixed solution had a trihydroxystilbene concentration shown in the table and 0.
4 shows a T rp -P-1 concentration of 4 mg / ml. The results of the above tests are shown in Table 1.

【0012】 表 1 −−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−− β−ガラクトシダーゼ活性 抑制率(%) −−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−− コントロール 176 ── トリヒドロキシスチルベン液(0.4mg/ml) 168 ── 活性化Trp−P−1液(0.4mg/ml) 423 ── −−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−− 活性化Trp−P−1/トリヒト゛ロキシスチルヘ゛ン混合液 0.4mg/ml 181 98.0 トリヒト゛ロキシスチルヘ゛ン濃度 0.3mg/ml 245 72.1 0.2mg/ml 280 57.9 −−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−Table 1 -------------------------------------------. Beta.-Galactosidase activity inhibition rate (%) −−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−− Control 176 ──Trihydroxystilbene solution (0.4 mg / ml) 168 --Activated Trp-P-1 solution (0.4 mg / ml) 423 ---------------------------------. -------- activated T rp -P-1 / Torihito Bu Rokishisuchiruben mixture 0.4 mg / ml 181 98.0 Torihito Bu Rokishisuchiruben concentration 0.3mg / ml 245 72.1 0.2mg / ml 280 57.9 −−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−−

【0013】上記表1に示すように、トリヒドロキシス
チルベンの濃度はSOS反応抑制率に対して正比例の関
係を示し、特にその濃度が0.4mg/mlの場合は、
抑制率が98.0%にまで向上した。これにより、トリ
ヒドロキシスチルベンが、活性化Trp−P−1によるS
OS反応の誘導に対して、強い抑制作用を示すことは明
らかである。尚、本発明においては、前記具体的実施例
に示すものに限らず、目的、用途に応じて本発明の範囲
内で種々変更した実施例とすることができる。即ち、ト
リヒドロキシスチルベン濃度は0.4mg/mlを越え
てもよいし、また溶液とするための溶媒も水に限らず、
目的等によっては他の溶媒、又は混合溶媒を用いること
ができる。更に、使用溶液には、種々の添加剤を配合す
ることもできる。
As shown in Table 1 above, the concentration of trihydroxystilbene is directly proportional to the SOS reaction inhibition rate, and particularly when the concentration is 0.4 mg / ml,
The suppression rate improved to 98.0%. This causes trihydroxystilbene to undergo S by activation T rp -P-1.
It is clear that it has a strong inhibitory effect on the induction of the OS response. The present invention is not limited to the specific examples described above, and various modifications may be made within the scope of the present invention depending on the purpose and application. That is, the concentration of trihydroxystilbene may exceed 0.4 mg / ml, and the solvent for forming the solution is not limited to water,
Other solvents or mixed solvents may be used depending on the purpose. Further, various additives may be added to the use solution.

【0014】[0014]

【発明の効果】以上のように、3−4’−5−トリヒド
ロキシスチルベンを含む物質は、構造が簡単で且つ優れ
た変異原抑制抑制作用を有している。従って、これは制
癌物質として充分に期待できる。そして、このトリヒド
ロキシスチルベン濃度が0.3mg/ml以上の場合
は、SOS反応抑制率が70%以上を示し、極めて優れ
た効果を有している。
INDUSTRIAL APPLICABILITY As described above, the substance containing 3-4'-5-trihydroxystilbene has a simple structure and an excellent suppressive effect of suppressing mutagen. Therefore, it can be sufficiently expected as a carcinogen. When the trihydroxystilbene concentration is 0.3 mg / ml or more, the SOS reaction inhibition rate is 70% or more, which is an extremely excellent effect.

Claims (2)

【特許請求の範囲】[Claims] 【請求項1】 3,4′,5−トリヒドロキシスチルベ
ンからなることを特徴とする変異原抑制作用を有する物
質。
1. A substance having a mutagen inhibitory action, which comprises 3,4 ′, 5-trihydroxystilbene.
【請求項2】 上記3,4′,5−トリヒドロキシスチ
ルベンの濃度が0.3mg/ml以上である請求項1記
載の変異原抑制作用を有する物質。
2. The substance having a mutagen inhibiting activity according to claim 1, wherein the concentration of the 3,4 ′, 5-trihydroxystilbene is 0.3 mg / ml or more.
JP4083370A 1992-03-05 1992-03-05 Mutagen inhibitor Expired - Fee Related JP2562092B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP4083370A JP2562092B2 (en) 1992-03-05 1992-03-05 Mutagen inhibitor

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP4083370A JP2562092B2 (en) 1992-03-05 1992-03-05 Mutagen inhibitor

Publications (2)

Publication Number Publication Date
JPH0624967A true JPH0624967A (en) 1994-02-01
JP2562092B2 JP2562092B2 (en) 1996-12-11

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ID=13800542

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Country Status (1)

Country Link
JP (1) JP2562092B2 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999056737A1 (en) * 1998-05-05 1999-11-11 Institut National De La Sante Et De La Recherche Medicale (Inserm) Arylhydrocarbon receptor ligand antagonists
CN1055859C (en) * 1997-04-16 2000-08-30 中国人民解放军空军总医院 Application of stilbene compound and its derivative in preparation of endothelium element antagonist agent

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6438009A (en) * 1987-07-31 1989-02-08 Pola Chem Ind Inc Beautifying cosmetic

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6438009A (en) * 1987-07-31 1989-02-08 Pola Chem Ind Inc Beautifying cosmetic

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1055859C (en) * 1997-04-16 2000-08-30 中国人民解放军空军总医院 Application of stilbene compound and its derivative in preparation of endothelium element antagonist agent
WO1999056737A1 (en) * 1998-05-05 1999-11-11 Institut National De La Sante Et De La Recherche Medicale (Inserm) Arylhydrocarbon receptor ligand antagonists
FR2778337A1 (en) * 1998-05-05 1999-11-12 Inst Nat Sante Rech Med ARYLHYDROCARBON RECEPTOR LIGAND ANTAGONISTS

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